


Lookout

by SpicyReyes



Series: lookout [1]
Category: Red Dead Redemption (Video Games)
Genre: Dom/sub, Dubious Consent, M/M, Oral Sex, Orgasm Delay/Denial, Teasing
Language: English
Status: Completed
Published: 2019-06-26
Updated: 2019-06-26
Packaged: 2020-05-20 04:10:42
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,411
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19369507
Author URL: https://archiveofourown.org/users/SpicyReyes/pseuds/SpicyReyes
Summary: Dutch ain't the only one capable of 'plans.'





	Lookout

**Author's Note:**

> this is for the broke dick mountain  
> xoxo

This was not his best idea. 

Granted, Bill's ideas were rarely great, but usually he could excuse them on heavy drinking. Tonight, though….tonight he'd kept it light, gone to bed early, and woke when the moon was at its highest to claim his prize. 

It had taken them a long time to trust the O'Driscoll to keep an eye out for their camp, but they'd done it, and tonight their safety was in the boy's shakey little hands. 

Bill, obviously, thought this was a brilliant opportunity. 

He crept through the woods, a grin on his face. His mouth was dry and head achey from the alcohol he'd mostly slept off, but they were distant nuisances under the excitement of his (admittedly loose) plan. 

Kieran's back came into view between a few trees some paces ahead, and Bill eased forward, footsteps as light as he could keep them. He still made enough noise for Kieran to stiffen, but he looked around the woods in front of him instead of turning, still under the impression any threats would come from the front. 

Bill reached out, clasping a large hand down on the back of Kieran's neck, pushing his head down. 

Kieran let out a startled, strangled noise, and pushed back against his heavy grip, pointing his gun wildly over his shoulder. 

"Watch it," Bill growled, pushing the barrel of the gun away. His hand snaked forward, coming around to grip the front of Kieran's throat instead, dragging him backward a step until he was stumbling into Bill's grasp completely, back smacking against the man's larger frame. 

"M-Mr. Williamson," Kieran stuttered out. "I-I'm meant to be on watch, um, sir, I ain't- I ain't doin' nothin' wrong, just lemme go. Please."

"You ain't a very good lookout," Bill said, stepping up to be flush against Kieran's back, leaning his head down to the man's shoulder to speak close and quiet in his ear. "Can't even tell which direction a sound's coming from. Really sloppy, O'Driscoll."

"I  _ ain't  _ an O'Driscoll," Kieran said, slightly firmer. "Let me go."

"Heh," Bill laughed. "Showin' some balls there, kid. Maybe I shoulda taken 'em when I had the chance."

"Sir, if someone comes-..."

"You'll see 'em," Bill assured him. "Long as you're payin' attention. Eyes out in the woods, ears open...no distractions."

He pressed back with the hand on Kieran's throat, applying gentle pressure, and rested the other hand on his hip. 

"W-what are you…"

"Eyes front, O'Driscoll," Bill reminded him, and brought the hand on Kieran's hip forward, splaying against his stomach. "Anyone manages to sneak into camp, I'll take more than just the pretty bits."

Kieran's Adam's apple, pressed hard against Bill's palm, bobbed as he swallowed. 

"You hearin' me, brat?" Bill prompted. His fingers turned slightly downward, their tips resting against the leather of Kieran's belt. "You gonna be a good boy and keep yer eyes open?"

More bobbing beneath his hand, and Bill paused, waiting eagerly for the response. He had a million ideas for what to do when Kieran argued, when Kieran refused-

-but after a long pause of silence, Kieran breathed out a strained, "Yessir."

The surprise of it didn't throw Bill long. He chuckled, pressed ever closer, and dipped his hand down, closing around Kieran's belt buckle, popping it free.  

"Good, good," he purred, loosening the belt. "You might be of some use after all, O'Driscoll. 

"I ain't-..Ah!"

Bill had grabbed the waistband of Kieran's pants, digging his thumb down all the way against the skin to grab every layer of fabric, and he pushed down harshly to drag it all down. Only using one hand meant it was not particularly effective, but the trousers dropped to mid-thigh, and the drawers beneath bunched up at the waistband and caught halfway down his ass cheeks, the bit directly under Bill's thumb coming all the way down just far enough to free a soft, modest pink cock. 

Bill stepped forward so that he was pressed flush against Kieran all the way down, causing the boy to stumble a bit, only to be dragged right back and pulled tight to Bill's chest by his throat. Slotting their legs together in a staggered pattern, Bill angled his hips so as to press a stirring erection against Kieran's hip. 

Even through Bill's trousers, the pressure was distinguishable, and Kieran barely bit back his whimper. Another shift of Bill's hips ground the mass in, giving some of the friction needed to fill it out all the way, and Kieran shut his eyes reflexively. 

Bill's hand moved from Kieran's waistband in an instant, coming up to cup his package, squeezing down on it harshly. Kieran let out a pained noise, eyes flying open in the shock of it, and was rewarded with the grip loosening, until Bill's hand was simply resting in an arc against him. 

"Eyes  _ open _ , boy," Bill reminded him. 

"Y-yessir."

This was the correct response, apparently, because Bill's hand moved again. His palm pressed in, fingers curling around the entire shape of him, cock and balls all gather together in one large hand. 

"There you go," Bill murmured, and began to toy with him, rolling him around in his palm as he began to stiffen. "You're figuring it out. You're not being relieved. You're gonna do your job...but, all work, no play, right?"

Kieran's dick, grown beneath its attentions, was no longer the malleable form that could be squished about lazily. Instead, Bill raised his hand, cupped over Kieran's genitals still, and moved palm back, dragging the tips of his fingers forward along the skin. Just over an inch forward, and his balls were free of the hold, dropping back down against the bunched waistband of his drawers. 

Bill kept his hand moving until he had Kieran's dick held straight up by the tips of his fingers, resting gently just below the head. 

Bill chuckled again, and moved his head, teeth grazing Kieran's ear. "Didn't take long," he teased in a husky whisper. "You rather play around, boy? Rather have fun than do real work, hm?"

Kieran heaved heavy breaths, forcing his eyes to remain fixed on the trees before him, though they kept unfocusing and were desperately begging to be shut. 

The grip moved after a moment, Bill's hand dropping down to surround Kieran's erection, squeezing down again. "I asked you a question, boy. You tryin' to get out of work?"

"N-no sir."

"I don't believe you," Bill said, but his touch lightened, and he dragged his hand slowly and teasingly along the length within it. "Look at you. You'd do anything not to have to keep an eye out." He caught Kieran's earlobe in a nibble, then let it drop free, saying in what was little more than a breath, "You'd prob'ly let me fuck you."

"N-no!"

"No?" Bill echoed. His hand slid slowly back down along his shaft. "You wouldn't let me fuck you? Or you ain't tryin' to get out of work?"

"I-..." Kieran swallowed. The hand around his neck tipped his head backward. "I...I ain't afraid to work. I'll earn my place."

"Your place?" Bill echoed, almost in a laugh. "I got a place for you."

The hand on his dick left him, causing him to let out a soft noise that was just shy of a whine, and both hands moved to his shoulders instead, spinning him around and pushing him to the ground. 

"I'll keep watch for a bit," Bill said jovially. "You, boy…" 

He unlatched his belt. Kieran, on his knees, swallowed nervously as Bill pulled loose his own dick, thick and curved in a sinful way. 

"Your watch is almost over," Bill said. "If you wanna make sure no one knows I had to do it for you...you better get workin'."

Kieran blinked, swallowed again, and then raised a hand, tentatively touching the side of the cock in his face. 

Bill's foot moved forward, the toe of his book tucking under Kieran's dick to rest ever so lightly over his balls. "Hands on your knees, boy."

Kieran quickly moved to obey, gripping the bunched fabric of his trousers at the lowest point of his thigh. 

Bill's hand came down, grabbing his own dick to steady it, and ordered, "Time to see if that mouth is worth all the trouble it took to get it open."

Kieran took a deep, anxious breath, and then leaned forward, mouth open, to very gently rest his mouth around the head of Bill's cock. 

It was thick enough to be uncomfortable for his jaw, and he was taking sharp deep breaths through his nose almost immediately, because he couldn't breathe through his mouth around it. 

Just as he was adjusting to the sensation of the tip of a dick in his mouth, though, Bill let out a frustrated huff. The man's other hand came around, fisting in the back of Kieran's hair and pulling, dragging him harshly forward until about two inches of the length were crammed into Kieran's mouth. 

The pressure against the roof of his mouth was alien to him, his jaw felt ready to crack under the stretch, and Bill gave him barely a second to register the feeling when he was pulled again. This time, the cock plunged back, and Kieran felt stretching and straining as some unknown length of it managed to force itself in, brushing harshly against the back of his throat. 

He gagged and choked as Bill yanked him backward, breaking him loose to cough and sputter, struggling to regain breath. 

Bill let out a low, rumbling laugh, but allowed Kieran to recover. As soon as he was able to breathe, though, his mouth was in use again, stretched around slightly more of it than the initial couple inches. 

Once more, he was held there for a second, then dragged forward, the cock plunging down until Kieran could feel the soft curls around the base brushing his lip, and then pulled backward. He wasn't freed this time, though - he was returned to the start, given a fraction of a second to recover there, and pulled again. 

Back and forth he was taken and eased away, until the motion became all-encompassing, Kieran barely able to spare the attention to keep himself breathing through his nose. The strain of this and the ache of his jaw combined to send tears rolling down his face, which in turn stuffed up his nose just enough to add a whole new layer of difficulty to his breathing. 

He let out a strangled noise around the length in his mouth, and was surprised when he was pulled free immediately, head being tipped back until he was looking up at Bill. 

The hand from the man's cock came forward to catch under his chin, a thumb swiping across a tear-stained cheek. 

"Aw, poor baby," Bill cooed. "Too much, hm? I'll tell you what." The hand in his hair, tugged once, then detangled and ran through the strands, practically petting. "I'll let you try again. Do it proper, this time, though, or I'm takin' over again, you got me?"

Kieran, still breathing heavily and harshly, managed a single, sharp nod. 

"Good, good," Bill cooed down to him, sounding only mostly mocking through the husk of clear arousal. He held his cock steady again, and guided Kieran's head forward to take it into his mouth again. 

Kieran took the few spare inches he was now reasonable able to manage into his mouth, and tried to think of how  _ he  _ liked this done, from the other end. Experimentally, he pressed his tongue up along the bottom of it, and was rewarded with the petting of his hair starting up again. 

Oddly comforted by this, Kieran grew braver still, and moved himself forward slowly, trying to gauge roughly how far he could take himself without creating that suffocating pressure on his throat. The answer was just over half of the length, its thickness the primary struggle, and Kieran moved his head, dragging himself up and down between these two safely determined zones. 

The hand in his hair was light and growing lighter, almost absent - almost  _ bored.  _ Something in him rallied against this, defiant, and he tried something new - he hollowed his cheeks a bit, adding pressure, and dragged his tongue along the flesh of the cock in an imitation of a whore from Lemoyne he would swear up and down he'd never met. 

The hand stopped, fingers curling in his hair, and a soft swear dropped from Bill's lips. 

Kieran found this oddly satisfying, like a victory, and did it again. The fingers curled tighter, and so Kieran moved his tongue a different way, than another, taking each positive reaction as cue to try something new. 

"Fuck, fuck-  _ shit,"  _ Bill swore above him, and Kieran felt a new sensation - a pulsing of the flesh his lips were stretched around. At first, he didn't even realized what had happened, too focused on his task. He'd felt something hit the back of his throat and swallowed without thought, and it wasn't until he was being dragged off a twitching cock by a harshly swearing Bill that he realized that had been cum. 

They both stayed where they were, panting, Bill's hand still in Kieran's hair and Kieran's hands still obediently clenched at his thighs. 

When the man above him made no move to do or say anything, Kieran raised a hand, bringing it toward his own crotch. 

The boot still resting on his balls pressed down very lightly, causing more discomfort than pain, but clearly a warning. Kieran paused in mid-movement, hand hovering in the air a moment, before he lowered it back to his knee. 

"Good boy," Bill muttered, almost distractedly, the hand petting his hair again. "You leave that."

"I-...?"

"You  _ leave it,"  _ Bill growled, hand clenching around his hair again to tip his head back, so that they were looking each other in the eye. "You don't touch it, or I'll  _ know." _

Kieran wasn't sure what made him breathe out, "..A-and?"

The toe against him pushed in for the briefest second of pain, before it moved away completely. So did the hand in his hair, and before he could react, Bill was backing away, tucking himself back into his trousers casually. 

"You touch that," Bill said, "and you're the only one who ever will."

He turned and walked away, but not before Kieran swallowed and managed a breathless, "Yessir."


End file.
